Higher transmission loss diminishes the performance of optical communication-be it the rate at which classical or quantum data can be sent reliably, or the secure key generation rate of quantum key distribution (QKD). Loss compounds with distance-exponentially in an optical fiber, and inverse-square with distance for a free-space channel. In order to boost classical communication rates over long distances, it is customary to introduce regenerative relays at intermediate points along the channel. It is therefore natural to speculate whether untended regenerative stations, such as phase-insensitive or phase-sensitive optical amplifiers, could serve as repeaters for long-distance QKD. The primary result of this paper rules out all bosonic Gaussian channels to be useful as QKD repeaters, which include phase-insensitive and phase-sensitive amplifiers as special cases, for any QKD protocol. We also delineate the conditions under which a Gaussian relay renders a lossy channel entanglement breaking, which in turn makes the channel useless for QKD.